Novel Routes to Bis-furan Diacids, Dialcohols, and Diamines:
Building Blocks for Renewable Materials

"Building Blocks" - example of thermoset polymer

(Children’s building blocks are a classic example of thermoset polymers – Image by TheresaMuth from Pixbay)

Opportunity

Available for Licensing
TRL: 6

IP Status

​US Utility Patent: US 9840485

Inventors

​Eugene Chen
Lu Wang
Yugi Eguchi

At A Glance

Researchers at Colorado State University have patented the novel synthesis of bisfuran diacids, dialcohols, and diamines using a bisfuran dihalide. These products are key intermediates leading to bio-furan-based resins or related polymeric materials.

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Reference No.: 16-095

Background

In recent years, technical development of bio-based polymers produced from renewable biomass as a raw material is in progress to reduce consumption of fossil fuels (such as petroleum and coal) to thereby contribute to mitigation of global warming.  As the monomer materials in obtaining bio-based polymers, bisfuran compounds (polymerizable monomers) have attracted much attention as bio-based raw materials due to their appealing structure. However, bisfuran compounds (such as bisfuran diacid, dialcohols, and diamines) require different intermediates for synthesis.  Thus, a common intermediate is desired to streamline the overall process of synthesizing various bisfuran compounds.

Technology Overview

A bisfuran dibromide has been established as the versatile and common intermediate for the high-yield synthesis of the three important classes of bisfuran monomers for furan-based renewable materials, bisfuran diacids, diols, and diamines.

The general synthetic route involves a coupling reaction of 2-methylfuran with a ketone (acetone or cyclohexanone) under acidic conditions and a bromination reaction of the resulting bisfuran dimethyl compound to produce the bisfuran dibromide intermediate. This dibromide intermediate is subsequently converted to the corresponding bisfuran diacid (via oxidation reaction with KMnO4 under basic conditions), bisfuran diol (by hydrolysis reaction under mild basic conditions), and bisfuran diamine (through the Gabriel reaction).

The versatility of the bisfuran dibromide intermediate and the effective transformation into the monomers with high to quantitative yield typically without the need for further purification highlight the two attractive features and potential for large-scale production.

Benefits
  • bisfuran dihalide is a common intermediary for the synthesis of various bio-based bisfuran compounds
  • high to quantitative yield without the need for further purification
  • High potential for large-scale production
Applications
  • Synthesis of various bio-based bisfuran compounds
  • Various biobased polymers derived from bisfuran monomers, such as polyesters, polyimides, epoxy thermosets, polyazomethines, poly-(esteramide)s, polyureas, etc.

Last updated: June 2021

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